Chicago Sightseeing Tours & Cruises tours

Chicago Sightseeing Tours & Cruises - Page 5

84 experiences to discover

Air & Helicopter Tours City & Sightseeing Tours Cruises & Sailing Tours Cultural & Theme Tours Day Trips & Excursions Private & Custom Tours Walking & Biking Tours

Explore the best sightseeing tours & cruises tours and activities in Chicago. Our unbiased ratings help you find the perfect experiences for your trip.

Sort by:

4.44

Chicago Downtown Food and Sightseeing Bike Tour

$59-$79

Taste iconic Chicago foods like deep-dish pizza

Bicycle and helmet

4.4

Chicago Historic Skyscrapers Walking Tour

From $35

Experience Chicago's iconic skyscrapers

Certified docent from the Chicago Architecture Foundation

4.37

Chicago Ghost Tour: Wind and Souls Adults Only

From $35

Feel your spine tingle with tales of gangsters

A spooky and historically accurate tour with a local guide

4.31

Chicago Lake and River Architecture Cruise

$44-$45

Explore Chicago's iconic architecture with expert guides

1.5-hour cruise on the Chicago River and Lake Michigan

4.23

Chicago Mimosa and Bloody Mary River Cruise

$41-$50

Sip refreshing mimosas and Bloody Marys

Cruise along the Chicago River

4.23

Chicago River Architecture and Hop-on Hop-off Bus Tour

From $99

Journey through vibrant Chicago streets

75-minute architecture river cruise

4.11

Chicago Night Driving Tour with Skydeck and River Cruise

$189-$204

Admire panoramic views from the Skydeck

Complimentary hotel pick-up and drop-off in Downtown Chicago

4.06

Chicago River Brunch Cruise

$94-$116

Savor a chef-prepared brunch

Narrated tour with ambient music

4.06

Chicago Underground Pedway Walking Tour

From $35

Explore hidden corridors and stained glass

Expert guide

4.06

Chicago Architecture River Cruise

From $39

Cruise along all three branches of the Chicago River

Pet-friendly

4.04

Chicago Lake Michigan Buffet Cruise

$176-$245

Savor a delicious buffet with freshly prepared dishes

Buffet with entrees, salads, and desserts

3.99

Chicago Art Deco Skyscrapers Walking Tour

From $35

Discover Art Deco origins and motifs

Admission to Chicago Architecture Center exhibits